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9 days
from US $2170
Sale price from US $1,953

Buena Vista Sailing Club

Cuba

Get ready to step back in time and party like it’s 1953. Hang in Havana, get serenaded in Santiago, play in pretty Camaguey, haggle your heart out and sprawl on the beach...

7 days
from US $1355
Sale price from US $1,220

Here comes the boom

British Virgin Islands

Life sounds pretty good when your biggest problem is deciding which deserted island to sail to next, but this isn’t a strange far-off mirage. Just whip out your swimsuit...

7 days
from US $1470
Sale price from US $1,323

High Thai'd

Thailand

Sailing the tropical waters around Thailand obviously makes for a terrible holiday. White sand beaches, limestone half pipes, snorkeling, waterfalls, swimming, cocktails...

9 days
from US $510

My Camel Humps

Egypt

Cairo is your kickoff point, check out the Pyramids and Sphinx while you’re in the area. Head on to Aswan for temples, bazaars and a felucca sailboat or camel ride, next...

8 days
from US $1460
Sale price from US $1,314

No Man Is An Island

Greece

 

Sailing is traditionally a pretty awesome thing to do. It’s relaxing, involves lots of lounging around and probably a fair bit of eating and drinking. Pirate jokes are also commonplace. The Cyclades is traditionally...

8 days
from US $1420
Sale price from US $1,278

Taking the Mykonos

Greece

Strut your way about Mykonos before making sail to Naxos and its beautiful beaches, old towns and older still ruins. Splash about in the waters of the Small Cyclades and dine...

10 days
from US $1850
Sale price from US $1,110

Poseidon's Playground

Greece

Get into the Mediterranean swing of things by pottering about Santorini, scoffing down saganaki and knocking back ouzo. See heaps-old towns, villages and monasteries in Amorgos...

8 days
from US $1425
Sale price from US $1,283

Brac to the future

Croatia

 

Things we love about this trip: The cats in Korcula; the plum festival in Blace; the beaches, cheese and wine in Brac; the beautiful people and beautiful pizza in in Hvar; the bureks in Split and the ocean off the edge of...

8 days
from US $1425
Sale price from US $1,283

H'var Good Time

Croatia

 

Aside from being a clever pun, the name of this trip isn't just a suggestion. It's a dead cert. That is of course unless you're not a fan of sailing,...

7 days
from US $1210
Sale price from US $1,089

Anchored in Amalfi

Italy

Board thy sturdy vessel in Procida and set sail for the Phlegrean Islands. Stop in at Sorrento and pop over to Pompeii. Chomp down on pizza in Naples, wander among olive groves...